Lead Benefits Analyst Americas

Cloud Software Group is seeking a detail-oriented and service-focused Senior Benefits Analyst to support the administration and operations of employee benefit programs across the Americas, including the United States, Canada, Brazil, Colombia, and Costa Rica. This role is responsible for accurate and timely benefits administration, employee enrollment and eligibility, vendor coordination, invoice reconciliation, compliance support, and employee service delivery. The Senior Benefits Analyst will independently manage assigned operational activities, research and resolve administrative issues, analyze benefits data, and identify opportunities to improve processes and operational efficiency. The position will collaborate closely with the Global Benefits team and cross-functional partners, including HRIS, Payroll, Finance, HR Business Partners, Legal, brokers, carriers, and third-party administrators. 1. Americas Benefits Administration • Support day-to-day administration of medical, dental, vision, life, disability, wellness, and other employee benefit programs across assigned countries. • Process and validate employee enrollments, new hires, terminations, qualifying life events, dependent changes, and eligibility updates. • Monitor benefit elections, coverage effective dates, and employee contributions to ensure accurate administration. • Research and resolve discrepancies between Workday, payroll, carriers, and third-party administrators. • Maintain accurate employee benefit records, documentation, and administrative procedures. • Support benefit plan changes, employee transfers, and organizational changes. • Review and support the reconciliation monthly benefits invoices against employee eligibility, enrollment records, and applicable rates. • Partner with Finance, Payroll, and vendors to coordinate billing corrections, adjustments, credits, and refunds. • Support benefits budget tracking and financial planning. • Coordinate Leave of Absence administration across the Americas. • Administer and coordinate interactive medical accommodation requests, including documentation, employee support, and tracking. 2. Vendor & Employee Support • Coordinate day-to-day administrative activities with benefit carriers, brokers, and third-party administrators. • Track and resolve vendor inquiries, enrollment discrepancies, coverage issues, and service escalations. • Serve as a primary point of contact for employee benefits questions related to eligibility, enrollment, coverage, payroll deductions, and claims administration. • Research employee issues and coordinate with vendors and internal stakeholders to ensure timely resolution. • Support employee communications, FAQs, benefits education, and enrollment activities. • Monitor vendor service issues and escalate recurring concerns to Benefits leadership. 3. Compliance & Open Enrollment Support • Support benefits compliance activities, including ACA data validation, COBRA administration, Form 5500 support, required notices, and audits. • Maintain documentation and assist with internal and external benefits audits. • Monitor administrative deadlines and coordinate assigned compliance requirements. • Lead U.S. Open Enrollment • Support regional benefit renewals through assisting with Workday testing, enrollment reviews, carrier file reconciliation, and post-enrollment audits. • Support implementation of approved plan changes and employee communications across assigned countries. 4. Workday, Data Integrity & Process Improvement • Maintain and validate employee benefits information in Workday and applicable vendor platforms. • Perform routine data audits and reconcile Workday records against payroll and vendor information. • Support Workday benefits testing, system enhancements, vendor integrations, and issue resolution in partnership with Benefits leadership and HRIS team. • Maintain operational reports, standard operating procedures, process documentation, and administrative trackers. • Support assigned process improvement and automation initiatives. 5. Cross-Functional & Global Benefits Support • Partner with HR Business Partners, Payroll, HRIS, Finance, Legal, and the broader Global Benefits team to support effective benefits administration. • Provide operational assistance and support for data validation for specialized initiatives, including retirement benefits, EOR administration, leave-related benefits matters, and HRIS enhancements. • Support regional benefits projects and other operational priorities as assigned. • Maintain effective working relationships with internal stakeholders and external service providers. Required Qualifications • Bachelor's degree in Human Resources, Business Administration, Finance, or related field, or equivalent professional experience. • 5+ years of experience in employee benefits administration or benefits operations. • Strong knowledge of America's health and welfare benefits administration. • Experience supporting benefits operations across multiple countries is preferred. • Experience with employee enrollment, eligibility, vendor billing, invoice reconciliation, and payroll deductions. • Proficiency with HRIS systems, preferably Workday. • Advanced Microsoft Excel skills, including pivot tables, lookup functions, reporting, and data analysis. • Strong analytical, organizational, and problem-solving skills. • Ability to manage competing priorities and independently oversee assigned responsibilities. • Excellent communication, customer service, and cross-functional collaboration skills. • Ability to maintain confidentiality and appropriately handle sensitive employee information. Preferred Qualifications • Experience supporting benefits administration in the United States, Canada, Brazil, Colombia, and Costa Rica. • Familiarity with ACA, COBRA, HIPAA, ERISA, and applicable benefits compliance regulations. • Experience with benefits financial reconciliation, vendor management, and operational reporting.